EP2292572A1 - Procédé pour la séparation de composés aromatiques d'un mélange - Google Patents

Procédé pour la séparation de composés aromatiques d'un mélange Download PDF

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Publication number
EP2292572A1
EP2292572A1 EP09169647A EP09169647A EP2292572A1 EP 2292572 A1 EP2292572 A1 EP 2292572A1 EP 09169647 A EP09169647 A EP 09169647A EP 09169647 A EP09169647 A EP 09169647A EP 2292572 A1 EP2292572 A1 EP 2292572A1
Authority
EP
European Patent Office
Prior art keywords
ionic liquid
aromatics
stream
aromatic compounds
rich
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP09169647A
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German (de)
English (en)
Inventor
designation of the inventor has not yet been filed The
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to EP09169647A priority Critical patent/EP2292572A1/fr
Priority to PCT/EP2010/063037 priority patent/WO2011026975A1/fr
Publication of EP2292572A1 publication Critical patent/EP2292572A1/fr
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/04—Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/20—Nitrogen-containing compounds

Definitions

  • Ionic liquids are known in the art and are organic molten salts that are liquid at relatively low temperatures, suitably up to 150 °C. Suitable melting points may range from -100 to 100 °C, preferably from 0 to 80°C, most preferably below from 0 to 20 °C. Ionic liquids are generally known and described in, e.g., EP-A 1854786 , WO-A 01/40150 , US-B 7019188 , US-A 4359596 and the references cited in US-B 7019188 .
  • the cationic moiety of the ionic liquid advantageously comprises a quaternary nitrogen or phosphorus atom. Hence, ionic liquids comprise ammonium and phosphonium compounds.
  • Such compounds suitably comprise one or more organic substituent groups, in particular alkyl groups with 1 to 12 carbon atoms.
  • the phosphonium and ammonium moieties comprise three or four alkyl groups.
  • suitable ammonium and phosphonium groups include trimethylammonium, tetramethyl ammonium, triethylammonium, tetraethylammonium, triethylphosphonium and tetraethylphosphonium.
  • such moieties provide suitable ionic liquids. Since nitrogen-containing ionic liquids provide the better results, the ionic liquid preferably comprises a nitrogen-containing cationic moiety.
  • the cationic moiety is preferably selected from the group consisting of (N-R 1 )-pyridinium and 1-R 2- 3-R 3 -imidazolium, wherein R 1 , R 2 and R 3 are alkyl groups with 1 to 6 carbon atoms.
  • R 1 , R 2 and R 3 are alkyl groups with 1 to 6 carbon atoms.
  • the alkyl group is suitably linear.
  • Such pyridinium and imidazolium moieties may bear one or more further substituents.
  • the pyridinium moiety may contain one or more further hydrocarbyl, preferably alkyl substituents with 1 to 6 carbon atoms. If the pyridinium moiety contains more than one substituent the melting point of the resulting salt tends to increase to undesirable levels.
  • Preferred anions for use in the present invention include alkyl or haloalkyl methanamides (for example tristrifluoromethanesulphonylamide), alkyl or haloalkyl sulphonylamides (for example bistrifluoromethane-sulphonylamide, also referred to as bis(trifyl)imide or bistriflamide), alkyl or haloalkyl sulphates (for example methylsulphate and octylsulphate), alkyl or haloalkyl sulphonates (for example methanesulphonate, trifluoromethanesulphonate and dioctylsulphosuccinate), carboxylates (for example methanoate, ethanoate, benzoate and lactate), dicyanamide ([N(CN) 2 ]-), azolates (for example 1,2,4-triazolate), phosphates or phosphonates (for example dimethylphosphate and
  • Suitable conditions at which the contact of the aromatics-depleted aliphatic stream with the adsorbent takes place include a temperature of from 20 to 80 °C and a pressure of from 0.1 to 20 bar. It is evident that such a treatment is more energy-friendly than fractionation. This adsorption treatment also prevents thermal decomposition of the ionic liquid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP09169647A 2009-09-07 2009-09-07 Procédé pour la séparation de composés aromatiques d'un mélange Ceased EP2292572A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP09169647A EP2292572A1 (fr) 2009-09-07 2009-09-07 Procédé pour la séparation de composés aromatiques d'un mélange
PCT/EP2010/063037 WO2011026975A1 (fr) 2009-09-07 2010-09-06 Procédé pour la séparation de composés aromatiques à partir d'un mélange

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP09169647A EP2292572A1 (fr) 2009-09-07 2009-09-07 Procédé pour la séparation de composés aromatiques d'un mélange

Publications (1)

Publication Number Publication Date
EP2292572A1 true EP2292572A1 (fr) 2011-03-09

Family

ID=41507961

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09169647A Ceased EP2292572A1 (fr) 2009-09-07 2009-09-07 Procédé pour la séparation de composés aromatiques d'un mélange

Country Status (2)

Country Link
EP (1) EP2292572A1 (fr)
WO (1) WO2011026975A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100261945A1 (en) * 2009-04-08 2010-10-14 Samsung Engineering Co., Ltd. Method of separating aromatic compound from mixture containing aromatic compound and aliphatic compound
US20180187100A1 (en) * 2017-01-04 2018-07-05 Saudi Arabian Oil Company Hydrocracking process and system including separation of heavy poly nuclear aromatics from recycle by ionic liquids and solid adsorbents

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1296990A (fr) * 1961-08-07 1962-06-22 Shell Int Research Séparation de mélanges d'hydrocarbures liquides utilisant un solvant sélectif polaire normalement gazeux, liquéfié
US4359596A (en) 1981-08-03 1982-11-16 Exxon Research And Engineering Co. Liquid salt extraction of aromatics from process feed streams
EP0562815A1 (fr) * 1992-03-27 1993-09-29 Exxon Research And Engineering Company Séparation d'hydrocarbures aromatiques à partir de mélanges aromatiques/non-aromatiques
WO2001040150A1 (fr) 1999-12-01 2001-06-07 Akzo Nobel N.V. Procede d'extraction de composes aromatiques d'une phase aliphatique par utilisation d'un liquide ionique non neutre
US7019188B2 (en) 2002-06-14 2006-03-28 Nova Chemicals (International) S.A. Use of ionic liquids to separate olefins, diolefins and aromatics
EP1854786A1 (fr) 2006-09-04 2007-11-14 BP p.l.c. Liquides ioniques et leur utilisation dans des procédés d'extraction
US7344126B2 (en) 2005-02-24 2008-03-18 Zhejiang University Of Technology Equipment of multi-rotors zigzag high-gravity rotating beds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1296990A (fr) * 1961-08-07 1962-06-22 Shell Int Research Séparation de mélanges d'hydrocarbures liquides utilisant un solvant sélectif polaire normalement gazeux, liquéfié
US4359596A (en) 1981-08-03 1982-11-16 Exxon Research And Engineering Co. Liquid salt extraction of aromatics from process feed streams
EP0562815A1 (fr) * 1992-03-27 1993-09-29 Exxon Research And Engineering Company Séparation d'hydrocarbures aromatiques à partir de mélanges aromatiques/non-aromatiques
WO2001040150A1 (fr) 1999-12-01 2001-06-07 Akzo Nobel N.V. Procede d'extraction de composes aromatiques d'une phase aliphatique par utilisation d'un liquide ionique non neutre
US7019188B2 (en) 2002-06-14 2006-03-28 Nova Chemicals (International) S.A. Use of ionic liquids to separate olefins, diolefins and aromatics
US7344126B2 (en) 2005-02-24 2008-03-18 Zhejiang University Of Technology Equipment of multi-rotors zigzag high-gravity rotating beds
EP1854786A1 (fr) 2006-09-04 2007-11-14 BP p.l.c. Liquides ioniques et leur utilisation dans des procédés d'extraction

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANJAN S T: "Ionic Liquids for Aromatic Extraction: Are They ready?", CHEMICAL ENGINEERING PROGRESS, AMERICAN INSTITUTE OF CHEMICAL ENGINEERS, NEW YORK, NY, US, vol. 102, no. 12, 1 December 2006 (2006-12-01), pages 30 - 39, XP001539945, ISSN: 0360-7275 *
D SAHA, HEAT AND MASS TRANSFER, vol. 45, no. 4, 2009, pages 451 - 457
S T ANJAN, CHEMICAL ENGINEERING PROGRESS, vol. 102, no. 12, 2006, pages 30 - 39

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100261945A1 (en) * 2009-04-08 2010-10-14 Samsung Engineering Co., Ltd. Method of separating aromatic compound from mixture containing aromatic compound and aliphatic compound
US20180187100A1 (en) * 2017-01-04 2018-07-05 Saudi Arabian Oil Company Hydrocracking process and system including separation of heavy poly nuclear aromatics from recycle by ionic liquids and solid adsorbents
WO2018129022A1 (fr) * 2017-01-04 2018-07-12 Saudi Arabian Oil Company Procédé et système d'hydrocraquage comprenant la séparation de composés aromatiques polynucléaires lourds à partir de recyclage par des liquides ioniques et des adsorbants solides
CN110168057A (zh) * 2017-01-04 2019-08-23 沙特阿拉伯石油公司 加氢裂化方法和系统，其包括通过离子液体和固体吸附剂从再循环分离重质多核芳烃
KR20190104037A (ko) * 2017-01-04 2019-09-05 사우디 아라비안 오일 컴퍼니 이온성 액체 및 고체 흡착에 의한 재순환으로부터 중질 다핵 방향족화합물의 분리를 포함하는 수소첨가분해 공정 및 시스템
US10920157B2 (en) 2017-01-04 2021-02-16 Saudi Arabian Oil Company Hydrocracking process and system including separation of heavy poly nuclear aromatics from recycle by ionic liquids and solid adsorbents

Also Published As

Publication number Publication date
WO2011026975A1 (fr) 2011-03-10

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